Biodegradable functional polycarbonate nanoparticle carries for delivering molecular cargo

Abstract

Techniques regarding the transportation of molecular cargo across the BBB are provided. For example, one or more embodiments described herein can comprise a chemical compound to facilitate molecular encapsulation of the molecular cargo. The chemical compound can comprise a diblock copolymer having a molecular backbone comprising a polycarbonate structure and a polyethylene glycol structure. Also, the polycarbonate structure can be functionalized with boronic acid.

What is claimed is: 
     
       1. A method, comprising:
 conjugating a chemical compound to a copolymer via an acidity-sensitive covalent boronate ester bond, 
 wherein the copolymer comprises a polyethylene glycol, 
 wherein the copolymer comprises a first polycarbonate functionalized with boronic acid; and 
 covalently bonding an amino functional group to a second polycarbonate of the copolymer, 
 wherein the acidity-sensitive covalent boronate ester bond is formed between the boronic acid and a catechol moiety of the chemical compound, 
 wherein the chemical compound is apomorphine, 
 wherein about 75% of the copolymer is conjugated with the apomorphine, 
 wherein the conjugated chemical compound is characterized by a chemical structure: 
 
       
         
           
           
               
               
           
         
         wherein “m” corresponds to a first integer greater than or equal to 45 and less than or equal to 454, 
         wherein “x” corresponds to a second integer greater than or equal to 2 and less than or equal to 50, and 
         wherein “y” corresponds to a third integer greater than or equal to 2 and less than or equal to 50. 
       
     
     
       2. The method of  claim 1 , further comprising:
 introducing a base organocatalyst to the chemical compound and the copolymer to accelerate formation of the acidity-sensitive covalent boronate ester bond. 
 
     
     
       3. The method of  claim 2 , wherein the base organocatalyst is pyridine. 
     
     
       4. The method of  claim 1 , wherein the amino-functional group is a tertiary amine. 
     
     
       5. A method, comprising:
 transporting a molecular cargo across a blood-brain-barrier via a molecular encapsulation of the molecular cargo within a nanoparticle and a biologically triggered release of the molecular cargo from the nanoparticle, 
 wherein the nanoparticle is a copolymer comprising a first polycarbonate functionalized with boronic acid, 
 wherein the molecular encapsulation is established by a boronate ester bond formed between the boronic acid of the first polycarbonate and a catechol moiety of the molecular cargo, 
 wherein an amino functional group is covalently bonded to a second polycarbonate of the copolymer, 
 wherein the copolymer comprises a polyethylene glycol, 
 wherein the molecular cargo is apomorphine and about 75% of the copolymer is conjugated with the apomorphine, 
 wherein the biologically triggered release is established by a change in acidity, 
 wherein the copolymer conjugated with the molecular cargo is characterized by a chemical structure: 
 
       
         
           
           
               
               
           
         
         wherein “m” corresponds to a first integer greater than or equal to 45 and less than or equal to 454, 
         wherein “x” corresponds to a second integer greater than or equal to 2 and less than or equal to 50, and 
         wherein “y” corresponds to a third integer greater than or equal to 2 and less than or equal to 50. 
       
     
     
       6. The method of  claim 5 , further comprising:
 inhibiting, by the molecular encapsulation, oxidation of the molecular cargo. 
 
     
     
       7. The method of  claim 6 , wherein the transporting the molecular cargo across the blood-brain-barrier is a treatment for a neurodegenerative disorder. 
     
     
       8. A method, comprising:
 transporting a molecular cargo across a blood-brain-barrier via a molecular encapsulation of the molecular cargo within a nanoparticle and a biologically triggered release of the molecular cargo from the nanoparticle, 
 wherein the nanoparticle is a copolymer comprising a first polycarbonate functionalized with boronic acid to facilitate a boronate ester bond, 
 wherein the molecular encapsulation is established by a boronate ester bond formed between the boronic acid of the first polycarbonate and a catechol moiety of the molecular cargo, 
 wherein an amino functional group is covalently bonded to a second polycarbonate of the copolymer, 
 wherein the copolymer comprises a polyethylene glycol, 
 wherein the biologically triggered release is established by a change in acidity, 
 wherein the transporting the molecular cargo across the blood-brain-barrier is a treatment for a neurogenerative disorder, 
 wherein the molecular cargo is apomorphine, 
 wherein about 75% of the copolymer is conjugated with the molecular cargo, 
 wherein the copolymer conjugated with the molecular cargo is characterized by a chemical structure: 
 
       
         
           
           
               
               
           
         
         wherein “m” corresponds to a first integer greater than or equal to 45 and less than or equal to 454, 
         wherein “x” corresponds to a second integer greater than or equal to 2 and less than or equal to 50, and 
         wherein “y” corresponds to a third integer greater than or equal to 2 and less than or equal to 50. 
       
     
     
       9. The method of  claim 8 , wherein the biologically triggered release is established in a presence of an environment having an acidity of less than or equal to 6.8 pH.